


Never Have I Ever

by imamotherfuckingstarlord



Category: Supernatural
Genre: Anal, Double Penetration, F/M, Kissing, Multi, Sam Winchester - Freeform, Sastiel - Freeform, Threesome, castiel - Freeform, castiel x reader x sam, sastiel kiss, some - Freeform
Language: English
Status: Completed
Published: 2016-09-17
Updated: 2016-09-17
Packaged: 2018-08-15 11:43:00
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,791
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8054947
Author URL: https://archiveofourown.org/users/imamotherfuckingstarlord/pseuds/imamotherfuckingstarlord
Summary: Dean is out for the night, leaving the Reader, Sam and Cas alone to drink and play an innocent game of Never Have I Ever.





	Never Have I Ever

After you threw back the shot of whiskey and gently settled the glass back down, Castiel smirked as he brought his own glass to his lips. The whiskey went down smoothly and the two of you stared across the table at Sam, who shrugged and took his shot like a professional. The sound of the Black Keys played low in the background of the bunker library as the three of you sat together.  
“Alright, who’s next?” You question as your fingers grazed over the rim of the glass. Castiel passed around the bottle of Dean’s whiskey, letting you all refill your glass as you prepared for the next round.  
Sam straightened up in his seat, taking a moment to think before he came up with a good one. “Never Have I Ever had a threesome.” He said with a smirk. The hunter laughed, expecting both you and Cas to not take a shot. Castiel looked slightly confused, but it only took him a moment to realize what Sam had meant, to which he promptly leaned back into his seat, shot glass untouched. The two men looked to you and you shrugged lightly. With a smirk you raised your glass and took the shot. Sam and Cas both look shocked and a bit intrigued at your admission. “I’m very adventurous.” You sighed as you looked to the angel “Cas, it’s your turn.”  
The angel’s thoughts were still on your sexual escapades, until Sam said his name, “Right, okay. Never Have I Ever slow danced with someone.” The confession broke your heart as you glanced at him; Sam and you both quickly downing your drinks.  
Once you settled your glass down, you got up out of your chair and motioned for the angel to get up, “Come on Cas, we can’t have any of that.” Sam smiled, his cheeks rosy from the alcohol as the angel hesitantly stood up from his chair to join you. The song that comes on next was a slow one and you took Cas’ hand and pulled him away from the table. You slipped your hands around his neck and moved close to him as the angel leaned forward, his hands resting on your hips. His blue eyes smiled down at you, “This isn’t so bad, right?” He dipped his head down closer to you and pressed his forehead against yours. You felt his fingers grip the edge of your shirt, and lightly graze your back. “Not so bad.”  
Something seemed to awaken in you, to stir inside because without thinking, your lips moved to press against his. For a moment Cas is hesitant, but he quickly leaned into the kiss as your hands softy tugged the hair at the nape of his neck.  
Sam watched the two of you slow dancing together, his glass of whiskey in hand as he adjusted in his seat, because for some reason the scene set before him, had turned him on. It had Sam feeling anxious and full of want. He looked at the clock on the wall to check the time. Dean was out for the night bar hopping, trying his best to get laid. Sam looked back at the two of you and watched as Castiel’s fingers gripped the back of your shirt and he knew that maybe he didn’t have to go to some bar to get what he needed after all. He cleared his throat, causing the angel and you to break from the kiss.  
Several thoughts began to swim in your mind, different scenarios announced themselves as you felt your skin itching for the touch of hands, “You do know I can feel your desire, (Y/N). I can feel everything that you want“. Castiel’s lips against your ear raised a stirring inside you as your eyes wandered to Sam. “He wants it too. I can feel his desires as well”. The angel’s hands were at your face, turning your head to face him. In a rush his lips crashed into yours, his tongue opening you up to him. A moan escaped into the angel’s mouth as your body tried to stand as your knees buckled.  
Castiel moved his mouth from yours, your eyes watching as he motioned for Sam to join the two of you. The hunter stared at the angel and then you, thinking to himself and waiting for some kind of signal. “Sam, come here,” you called, your voice filled with such a desire that it nearly burned coming out of your mouth.  
Cas’ lips were on yours again as his hands ran down your body. You closed your eyes as you felt the trails of the angel’s kisses move down to your neck; his hand sliding around your waist as you leaned back into a sturdy chest.  
Sam drew down to kiss the other side of your neck as his hands slid up the front of your shirt. There were no words exchanged as Castiel pulled away, his fingers moving down to the edge of your hands and the two men slid your tee shirt up, pulling it over your head. The shirt was tossed to the ground as Sam worked from behind you to undo your bra; quickly slipping it off. The hunter cupped both of your breasts in his large hands as Cas worked to remove your jeans. Your body felt as if it were on fire, a thin layer of an aching itch that needed to be released.  
Sam continued to kiss your neck as he gave you a playful bite, “Fuck, Sam,” is all you can manage as your eyes wandered to the angel.  
Castiel removed his trench coat and let it fall to the ground as he smiled wickedly at you and knelt down. You felt Sam’s hand slowly moving down to the front of your jeans as his mouth bit down gently on your earlobe. You moaned loudly, as Cas unzipped your jeans, taking his time as he gently pulled them down to your knees. He settled back as he successfully removed them from your legs. His blue eyes shone up at you, a smirk on his face “I’m going to enjoy this” he said as your chest heaved as you watched him lean toward your thigh; his hands grazing the back of your leg, his fingers tips lightly kneading into your skin.  
Cas’ lips trailed up your thigh as Sam’s fingers moved to the edge of your black cotton underwear. You let out a whimper as Sam’s fingers gently massage over your clit “Cas, she’s nice and wet.” The tall man grunted into your hair as his fingers made a circular motion over your clit, causing you to lean back into him even more. You could feel his cock harden against your back and you moved your hands over your head and back around his neck.  
Cas removed your dampened panties with his fingers; the angel’s dick aching in his trousers. Your back arched as you stood fully naked; your head dizzy with pleasure. It was a sensory overload, having two pairs of hands on you at once.  
And then, without warning, Cas’ tongue was inside of you. He used his hands to spread your legs further apart and his tongue lapped at your insides, tasting your sweetness. “Cas..Cas.” you moaned as you removed your hands from Sam’s neck, moving to the tousled brown hair and tugging it roughly. You felt a low groan come from the angel as his tongue moved faster.  
You turned your head slightly and Sam kissed you for the first time; his lips moving desperately against yours. His hands greedily massaged your breasts, his calloused fingers pinching your nipples hard.  
“Hold on, Cas keep going,” Sam ordered, his touch leaving your skin and leaving you to focus on the angel on his knees. You stood there, trying to keep your balance, all while moving Castiel’s head closer into you.  
You heard the sound of a chair being dragged across the floor and turned to see Sam behind you. He settled down on the chair and motioned for you to set on his lap. He was close enough so that you just had to sit down; letting Cas continue his work of eating you out. Sam spreads his legs, your ass up against his clothed hard cock.  
Cas adjusted to the new position and placed one hand on your knee, the other on your breast. Sam’s hands are gripped your waist as he slowly moved you up and down on his crotch, trying his best to stay in rhythm with Cas. The two men moved into a working groove, leaving you to succumb to your urges.  
The angel could nearly taste your relief and he began to move faster, his tongue able to feel your walls bursting; the taste of you on his lips as your whole body shuddered in release. The angel kept his mouth on you until he was sure you’d given him everything.  
Your pussy felt oversensitive as Cas removed his mouth from you and licked his lips as he pulled from you. Sam continued to grind himself against your ass, his fingers digging into your hipbone.  
The angel got up from his knees, his eyes on you as he unbuckled his belt and pulled it from his pants, bringing the end to your skin. He slid the leather down your stomach, Sam keeping both his hands at your nipples as his mouth bit down on your neck. You whimpered from the touch of both men and when the angel brought the end of the belt down to your aching pussy, you couldn’t help but thrust your hips up toward it. The blue eyed man gave you a smirk as he gently but assertively tapped the leather belt against your pussy. He watched you crumble as you moaned in Sam’s arms. Your sounds had both men desperately wanting more.  
Sam nodded to Cas, “I think she likes that Cas, keep that nearby.” Castiel nodded at the hunter and turned to place the belt on the table. When he came back to you and Sam, he’s unbuttoned his pants and dragged them down to the floor and stepped out. His boxers could barely contain his throbbing hard on as you heard Sam fooling with his zipper. “Y/N, get up for a minute,”. You did what the hunter said, giving him a full view of your bottom.  
“Come here Cas, I’ll help you with that,” you said as your hand moved forward and you reached for the hem of his boxers. You teasingly let your fingers linger until the angel grunted and pulled you forward by the neck. He kissed you roughly, his tongue attacking yours.  
And then you felt two large warm hands on your ass. Sam took both cheeks in his hands and massaged them before he pulled you back down onto his lap. Castiel let out a small whimper as your lips left his.  
The surprising feeling of bare flesh against your body had you frozen until Sam’s arms were around your waist; his body warm and his cock up against your pussy. His length didn’t surprise you one bit as you reached down and softly gripped his tip. Sam moaned into your hair as his hips buckled up; his cock moving in your hand.  
The angel watched the two of you together before you moaned out his name and he moved closer to you. You pulled down his boxers to reveal his throbbing dick. “Fuck, Castiel,” you whispered. The angel’s dick had the girth and length you imagined that it would and you reached out to grab hold of it. Cas moved closer and you moved your hand up and down his shaft; slow at first until Sam had you by the hips once more, grinding you fast and hard against his cock.  
With Cas in your hand, you moved quickly, and the angel leaned his head back in pleasure. Sam straightened himself up and moved you with him; his lips kissed your ear as he spoke “ Take him in your mouth.” Sam’s voice was husky and low and sent chills down your spine.  
You gently brought Cas forward with your hand and he looked confused for a moment before your lips were around his tip. A low groan came from the angel as he placed a hand on your back to steady himself. You felt Sam’s hand move down to your clit and he rubbed gently as you took the angel into your mouth.  
The three of you found a steady rhythm and you moved your hands around to Castiel’s ass and rubbed it as you edged further down his cock.  
Sam placed soft kisses on your back and worked his way to the nape of your neck. “Fuck Y/N, you’re delicious.” You could feel Sam’s cock twitching against you and it began to drive you insane.  
You moaning as you slowly brought your lips up the angel’s cock to the tip and started to lap it with your tongue before opening your mouth again to take his cock back in. “I’m going to-” Cas doesn’t finish his sentence as he suddenly jerked forward and your mouth was filled with his release. He tasted sweet on your tongue and he had you wanting to taste it again. The hunter’s movements speed up underneath you, grinding his cock against your pussy, as the angel pulls from you. A low moan comes from Sam as he ejects all over your pussy and inner thigh. He slows down the motion of his body, letting you settle for a moment as you leaned against his chest, a smile on your face.  
Castiel stood there, his cock sprung up as he took off his remaining clothing. “Should we take this to your bedroom?” he asked. Sam and you both murmured a yes and suddenly the three of you were in your room. You all stood close, each of you waiting for the other to make the first move. And when you saw both men hesitating, you reached for Sam’s hand and pulled him against your chest. He leaned down to place a chaste kiss on your lips, his hands going straight to your pussy. You reached behind you, searching for the angel who took your hand and let you pull him into your back. You could feel Castiel’s cock against your backside as his hands moved over your breasts. You leaned into Cas’ chest and looked up at the hunter. Sam smiled before he got down on his knees. You put your full weight against the angel as Sam’s mouth started to devour the sensitive aching between your legs. A cry of pleasure erupted from your mouth and Castiel moved his mouth to your ear.  
“You like that honeybee? Come for him”. His deep voice only enhanced the pleasure you felt as his fingers gently played with your nipples.  
Sam worked with his tongue until you couldn’t handle it anymore. You wanted the two men so badly. You stopped the hunter in your eagerness “Sam, go sit on the bed” his hazel eyes met yours and you nodded before he stood to do what you told him to. You turned to face Castiel and kissed him gently “You too, Cas.” The angel took a seat next to the hunter, their cocks both hard as you knelt down in front of them.  
The ground was hard under your knees but it didn’t matter as you took both men in your hands. Whimpers come from the angel and hunter as your hands started to slide up and down their cocks and you watched them intently as they closed their eyes; Cas biting down on his lip while Sam’s hand gripped the comforter.  
You moved at the same tempo with each hand, their cocks twitching in your palms. “Cas, baby, open your eyes. You too, Sam.” Hazel and blue eyes met yours, hungry for more as you moved closer. You leaned down to kiss Sam’s thigh and trailed slowly towards the hunter’s cock. “Fuck,” Sam said as his hand went to your head and he combed through your hair. Your lips settled on the base of his dick, taking your sweet time moving upward toward the tip as you hears a growl comes from the man. His fingers tugged gently on your hair and you pulled away with a smirk on your face. “Now, Sammy. Be nice.”  
Castiel’s hand reached for your chin and pulled your attention to him; drawing you higher on your knees as the angel’s lips pressed against yours. You opened your mouth to him and felt his tongue slide in as you moaned into his mouth and moved your hand faster around his cock. With your lips still locked to Cas, you moved your left hand towards Sam who grabbed it and placed a kiss on each finger. You moved your hand up around his neck and pulled the hunter’s face closer to yours and Cas’. You gave the angel’s lips a nip as you moved away to Sam. While Cas’ kisses were soft, steady and full of need; Sam’s were rough, insistent and full of want.  
You moved back and forth between the two men until the three of you were mere inches from each other’s faces. Your hands held their necks and rubbed them gently as you edged them toward one another. The men hesitated, watching the other, but it was Cas who filled in the gap. His soft lips were pressed against Sam’s who faltered for a second before returning the kiss.  
Moving back, your hands started pumping both men, watching with rising arousal as Sam and Cas slowly edged into each other’s mouths.  
Castiel moved his hand to Sam’s neck and pulled him closer while Sam had his large hand on Cas’ face; their mouths opened and closed against one another.  
“Oh, fuck,” you muttered as you watched the two men kissing; feeling yourself getting wetter. A chuckle came from Sam’s mouth as he gave Cas a small peck and pulled away. You removed your hands from the men and stood up to take a seat in between them. The hunter tried to hide his flushed face by running his hand over it.  
“There’s a first time for everything, huh Sam?” The younger Winchester smiled sheepishly before he shrugged and rested his back down on the bed.  
A small kiss on your shoulder from Cas got the ball rolling and you turned to face him. His blue eyes darkened as he slowly pushed you down on the bed. “I can’t wait any longer” Cas stood up to moved in between your legs and he grabbed you by the waist and lifted you higher on the bed until his knees were settled. The angel took his cock and moved it to the opening of your pussy; your breath sharpened as you waited for him. He pushed himself in and filled you up. Cas paused a moment to give you time to adjust. A breathy moan from you signals to him to start moving. His limber fingers gripped your hipbone and pulled you closer to his cock, teasing you by moving in and out of your pussy; each time going deeper than the last.  
Your eyes wandered to Sam as his hands held his cock. “I have a mouth, Sam,” you said, and his hazel eyes narrowed as he got up from the bed and walked around to the other side to crawl onto the bed. He knelt to the left of you, his large cock full and hard, and inches from your mouth. You obediently turned your head to the left. With your mouth open wide, Sam slipped inside of you as Cas continued to slam his cock in and out your pussy. You moaned against Sam’s dick, feeling yourself reaching the breaking point with every thrust from the angel’s cock. “Faster, Cas. She’s almost there.” Sam brushed the hair from your eyes as he rocked his hips, fucking your mouth roughly. Cas’ hand palmed your breast as he moved down; his tongue licking away at your hard nipple. Your moan is muffled by the hunters cock in your mouth so you reached down and pushed Cas’ head closer to your breast. He looked up from his attention to your breast “You like that baby?” Nodding with a mouth full of Sam, your hips bucked underneath the angel.  
The men started moving faster, fucking you until your eyes rolled back and body shuddered; mouth full of Sam’s cum. The sound of heavy panting came from the three of you as both men pulled out of you.  
You licked your lips at the taste of Sam that lingered in your mouth; your chest heaving up and down as beads of sweat graced your forehead. You smiled up at both men as Cas took you in with his eyes. His hand moved down to your thigh and you felt a wave of grace removing any tiredness you had. “Sam, she’s ready for you,” Cas nods as he backs off from the bed. He stood back for a moment, watching intently as Sam moved off of the bed.  
“Y/N, get on your knees.” Sam’s voice was assertive but soft as you got on your knees across the bed. “Fuck, I already know you’re going to be tight” Sam’s hand cupped your rear, sending a vibration through your body, “Alright baby, I’m going to go slow at first and let you get used to it. But then“ Sam’s cock moved toward your ass, gently moving his tip to your entrance, “Then I’m going to go fast and rough. Is that okay?” Sam kissed the small of your back as his hand cupped your breast “Fuck, yes Sam. Please!” You practically begged him as you gripped a handful of the comforter.  
Castiel watched from a chair in the corner, pleasuring himself to the hunter entering you from behind and moving faster as your cries of pain and pleasure erupted from your throat.  
“Cas, come join buddy” Sam groaned as he eased himself further into your ass, giving you a healthy slap across your rear. “You’re so fucking tight. Cas she’s so tight.” Castiel smirked as he got on the bed, moving his cock directly in front of your face. Your hands were trembling as you tried to keep yourself up. Sam’s cock was fully inside of you as he pushed as far as he could into your rear, the pain had been replaced with pleasure.  
“Is she? Well, I’ll have to give it a try next, right baby?” Words could not be formed as the intense buildup from Sam slamming into your ass has rendered you speechless. All you could manage was a nod.  
Sam’s hands were gripping your wrist so tightly that you were sure there would be bruises the next day. But the weight of every push into you made up for it.  
Cas gently stroked your hair and tipped your head up with a finger “You’re so beautiful. So sexy. And-” Cas lowered his head to your ear as his deep voice came out dangerously low “And those lips. I want to fuck those lips until the end of times.” His words burned in your core as they erupted into a ball of deep arousal. “Do it, Cas, do it,” you cry out to the angel. Castiel doesn’t hesitate to take his cock in hand as you opened your mouth. On your hands and knees the hunter took you from behind; the sound of skin slapped as he pushed deep into you and on the other end, the angel was thrusting his hips into your mouth, as you deep throated his cock. Sam moved his fingers around your clit and made sure you felt the same pleasure that he and Cas felt.  
The three of you moved rapidly as you tried to reach the sweet release. Sam arrived first and you felt yourself being filled up as cum spilled out of your ass. The hazel eyed man gently pulled out, leaving behind a feeling of emptiness, as he continued to tease your clit.  
Cas arrived next and pulled out, coming on your lips; his taste still as sweet. And then it was you. Sam hit just the right spot and you let it all go on his fingers. You collapsed on your stomach and tried to regain your breath. Sam moved against the headboard and slid down onto a pillow.  
“Don’t tell me you two are tired now?” Cas shook his head as his fingers grazed your sensitive nipple. You and Sam laughed together “Sorry Cas, but Y/N and I are only human. We’re spent.” Cas’ eyes narrowed as he moved toward Sam and you on the bed “We can’t have that. I have a surprise for both of you,” the angel gave a sly smile as he touched both you and Sam with his hands, his grace blanketing over the two of you. All the aching from your body disappeared along with your sensitivity. You looked toward Sam and knew he felt it too. “Sam, trade places with me,” Castiel commanded, getting off the bed. Shooting a glance at Sam, he shrugged with a smile and pulled himself up. Cas took Sam’s place and motioned for you, “Come here and put your back on my chest,” with a intrigued smile, you let Cas pull you down to him. You felt his chest rise and fall underneath your back. “Sam, in front of Y/N.” You let your head fall back over Cas’ shoulder, he kissed your neck and pulled away as you waited for further instructions because it was evident now that the angel was in charge.  
“Honeybee, I’m going to enter you from behind. I promise to be gentle.” His whisper tickled your ear as he reached down with his hand and let his tip tease your entrance. “Go ahead Cas, I’m ready angel,” With your permission, the angel entered you. He held his breath going in until he was fully sheathed. He sighed heavily “You were right Sam, she’s so tight. Go ahead, it’s your turn,” Cas held himself in and waited for the hunter to enter you. Sam grabbed your legs and pulled them over your shoulders and stroked himself, hardening in his own hands before he entered you. “Sam, Cas, fuck me. Fuck me hard!” Your voice was trembling as both men filled your request. The sensation was disorienting as pleasure came from both men. You couldn’t even tell who was who.  
Their cocks moved deep inside of you and hit all the right spots. Sam could feel your walls clench around his cock and Cas couldn’t believe how nice and tight you were.  
The three of you moved in unison as your loud moans filled the bunker room. And then you felt it, the invisible air drifting over your body, digging deep into you, bringing satisfaction you’ve never felt. “Cas,” Sam moans out, the angel’s name coming from the Winchester stirred something inside of you and made you want to hear it again, but Cas’ grace had you in its grip.  
As the three of you edged closer to release, the movements of your bodies grew eager; the buildup was almost too much.  
Then it happened; a simultaneous explosion of gratified pleasure. Sam and Cas both thrust into you one last time and caused you to wither between them. The three of you stayed still and let your bodies rest in an entanglement of limbs.  
Sam finally kissed your legs before he removed them from off of his shoulders. Cas’ chest was heaving heavily underneath you and you let yourself slide off of him.  
The bed was soft as you rested against the pillow. Sam moved next to you and you leaned in and kissed him softly on the mouth and then turned to Cas and did the same. Soft laughter filled the room as you lay in between the men.  
“Well, that was interesting.” Cas smirked as he rested on his elbow facing Sam and you as a realization came over you. “Guys, we didn’t use Cas’ belt,” you laughed into the pillow as exhaustion washed over you. With a mischievous look, Cas took his hands and placed them on Sam and you and healed you once again. The angel jumped from the bed, fully naked “I’ll go get the belt. Round two?” The angel eyed the two of you and waited for an answer. Sam and you exchanged looks and laughed as Sam pulled you into his arms and smirked “Round two, Cas. Round two.”


End file.
